ES2101655A1 - Process for the preparation of N-methyl-3-phenyl-3-(p- trifluoromethylphenoxy)propylamine - Google Patents

Process for the preparation of N-methyl-3-phenyl-3-(p- trifluoromethylphenoxy)propylamine

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Publication number
ES2101655A1
ES2101655A1 ES09501530A ES9501530A ES2101655A1 ES 2101655 A1 ES2101655 A1 ES 2101655A1 ES 09501530 A ES09501530 A ES 09501530A ES 9501530 A ES9501530 A ES 9501530A ES 2101655 A1 ES2101655 A1 ES 2101655A1
Authority
ES
Spain
Prior art keywords
trifluoromethylphenoxy
phenyl
converting
reaction
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
ES09501530A
Other languages
Spanish (es)
Other versions
ES2101655B1 (en
Inventor
Almudena Rubio
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lilly SA
Original Assignee
Lilly SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lilly SA filed Critical Lilly SA
Priority to ES9501530A priority Critical patent/ES2101655B1/en
Publication of ES2101655A1 publication Critical patent/ES2101655A1/en
Application granted granted Critical
Publication of ES2101655B1 publication Critical patent/ES2101655B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Process for the preparation of N-methyl-3-phenyl-3-(p- trifluoromethylphenoxy)propylamine Consists of the following stages: Reacting benzaldehyde with allylmagnesium bromide to obtain 1-phenyl-3-buten-1- ol, converting this into 4-phenol-4-(p- trifluoromethylphenoxy) butene by reaction with 4- trifluoromethylphenol in the presence of triphenyl phosphine and diethyl azodicarboxylate, converting the product obtained into 3-phenyl-3-(p- trifluoromethylphenoxy) propanal by reaction with osmium tetroxide and sodium periodate, converting the product obtained into title product I by reaction with methylamine under conditions for the formation of the corresponding imine, and subsequent in situ reduction of the imine formed using sodium cyanoborohydride. Finally product I is converted into its hydrochloride by the addition of hydrogen chloride. The invention is of use in the advantageous industrial preparation of I.
ES9501530A 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE. Expired - Fee Related ES2101655B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ES9501530A ES2101655B1 (en) 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES9501530A ES2101655B1 (en) 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

Publications (2)

Publication Number Publication Date
ES2101655A1 true ES2101655A1 (en) 1997-07-01
ES2101655B1 ES2101655B1 (en) 1998-01-16

Family

ID=8291207

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9501530A Expired - Fee Related ES2101655B1 (en) 1995-07-28 1995-07-28 N-METHYL-3-PHENYL-3- (P-TRIFLUOROMETILFE NOXI) PROPYLAMINE PREPARATION PROCEDURE.

Country Status (1)

Country Link
ES (1) ES2101655B1 (en)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES433720A1 (en) * 1974-01-10 1976-12-01 Lilly Co Eli Arloxyphenylpropylamines
ES8707175A1 (en) * 1986-06-13 1987-07-16 Inke Sa N-Methyl tri:fluoro:methyl-phenoxy phenyl-propylamine prepn.
EP0369685A2 (en) * 1988-11-14 1990-05-23 Eli Lilly And Company Fluoxetine analog
EP0380924A1 (en) * 1989-01-10 1990-08-08 Grato Magnone Process for the preparation of fluoxetine hydrochloride
EP0391070A1 (en) * 1989-03-03 1990-10-10 Orion-Yhtymä Oy Fermion Process for the preparation of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenyl-propylamine and their salts
WO1994000416A1 (en) * 1992-06-26 1994-01-06 Richter Gedeon Vegyészeti Gyár Rt. Preparation of n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine and acid addition salts thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES433720A1 (en) * 1974-01-10 1976-12-01 Lilly Co Eli Arloxyphenylpropylamines
ES8707175A1 (en) * 1986-06-13 1987-07-16 Inke Sa N-Methyl tri:fluoro:methyl-phenoxy phenyl-propylamine prepn.
EP0369685A2 (en) * 1988-11-14 1990-05-23 Eli Lilly And Company Fluoxetine analog
EP0380924A1 (en) * 1989-01-10 1990-08-08 Grato Magnone Process for the preparation of fluoxetine hydrochloride
EP0391070A1 (en) * 1989-03-03 1990-10-10 Orion-Yhtymä Oy Fermion Process for the preparation of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenyl-propylamine and their salts
WO1994000416A1 (en) * 1992-06-26 1994-01-06 Richter Gedeon Vegyészeti Gyár Rt. Preparation of n-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propylamine and acid addition salts thereof

Also Published As

Publication number Publication date
ES2101655B1 (en) 1998-01-16

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